Ring Enlargement of N-Phosphanyl-1,2,3,4-tetrahydroquinazolines
We found that 1-phosphanyl-1,2,3,4-tetrahydroquinazolines undergo ring enlargement. Their treatment with trifluoroacetic or hydrochloric acid afforded diazaphosphepinium salts. Deprotonation of these salts gave the corresponding neutral diazaphosphepines. The reaction of 1-phosphanyl-1,2,3,4-tetrahydroquinazolines with diazomethane or phenylazide afforded triazaphosphocine derivatives via insertion of P-N moiety. At the same time, an analogous hexahydropyrimidine derivative reacted with phenylazide in a normal manner at the phosphorus atom to afford the P(V) derivative.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:85 |
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| Enthalten in: |
The Journal of organic chemistry - 85(2020), 22 vom: 20. Nov., Seite 14467-14472 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Marchenko, Anatoliy [VerfasserIn] |
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| Anmerkungen: |
Date Revised 20.11.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.joc.0c00750 |
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NLM314045805 |
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| 520 | |a We found that 1-phosphanyl-1,2,3,4-tetrahydroquinazolines undergo ring enlargement. Their treatment with trifluoroacetic or hydrochloric acid afforded diazaphosphepinium salts. Deprotonation of these salts gave the corresponding neutral diazaphosphepines. The reaction of 1-phosphanyl-1,2,3,4-tetrahydroquinazolines with diazomethane or phenylazide afforded triazaphosphocine derivatives via insertion of P-N moiety. At the same time, an analogous hexahydropyrimidine derivative reacted with phenylazide in a normal manner at the phosphorus atom to afford the P(V) derivative | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Hurieva, Anastasiia N |e verfasserin |4 aut | |
| 700 | 1 | |a Shishkina, Svitlana |e verfasserin |4 aut | |
| 700 | 1 | |a Rusanov, Eduard |e verfasserin |4 aut | |
| 700 | 1 | |a Kostyuk, Aleksandr |e verfasserin |4 aut | |
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